Iodoethane → 2-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinonitrile

HRID 353226Notes

Reaction equation

HRID 353226 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[N:12]=[C:11]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:10]([C:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][CH:19]=2)=[CH:9][C:6]=1[C:7]#[N:8].I[CH2:26][CH3:27]>CO>[NH2:4][C:5]1[N:12]=[C:11]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:10]([C:18]2[CH:23]=[CH:22][C:21](=[O:24])[N:20]([CH2:26][CH3:27])[CH:19]=2)=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 99654582-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 129921352-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinonitrileYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (155 mg, 2.87 mmol) was added to a suspension of 2-amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (400 mg, 1.44 mmol) in methanol (8 ml) at room temperature in a nitrogen atmosphere, followed by stirring. After 15 minutes, iodoethane (0.35 ml, 4.38 mmol) was added thereto, followed by stirring as it was. After 15 hours, additional iodoethane (0.35 ml, 4.38 mmol) was added thereto, and the mixture was further stirred. After 24 hours, the reaction solution was concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=2:1, 1:2, 1:5). The resulting crude objective compound was suspended in diethyl ether, and then the solid was collected by filtration and washed with diethyl ether, to give the title compound (149 mg, 34%) as a pale yellow solid.

Workup

  1. stirringby stirring as it
  2. waitAfter 15 hours
  3. waitAfter 24 hours
  4. concentrationthe reaction solution was concentrated
  5. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=2:1, 1:2, 1:5)
  6. filtrationthe solid was collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-58e6837cccab4f14945afe4002aaadc6
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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